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We reported palladium-catalyzed regioselective [3+2] cycloadditions of <i>α</i>,<i>β</i>-unsaturated imines with vinylethylene carbonates, providing the desired oxazolidines in moderate-to-high yields. This reaction provides a facile route for the highly regioselective synthesis of functional oxazolidines. The synthetic utility of the current method was also demonstrated by a gram-scale reaction.